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Amphiphilic Carbohydrate‐Based Mesogens, VIII. A Facile Synthetic Route to Mesogenic L‐ ribo ‐1,2,3,4‐alkanetetrols
Author(s) -
Dahlhoff Wilhelm V.
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199219920122
Subject(s) - chemistry , mesophase , amphiphile , yield (engineering) , mesogen , carbohydrate , palladium , carbon fibers , organic chemistry , catalysis , stereochemistry , polymer chemistry , copolymer , liquid crystalline , materials science , phase (matter) , composite material , composite number , metallurgy , polymer
The Wittig olefinations of 2,3‐ O ‐isopropylidene‐ D ‐ribofuranose ( 1 ) with two equivalents of alkylidenetriphenylphosphorane (alkylidene: hexylidene — undecylidene) followed by hydrogenation catalyzed by palladium on carbon and subsequent deprotection yield (2 R ,3 S ,4 S ‐(“ L ‐” ribo )‐1,2,3,4‐alkanetetrols 5 . These amphiphiles form the smectic A mesophase on melting. However, when 1 is heated with one equivalent of the alkylidenetriphenylphosphoranes for longer periods, (2 R ,3 S ,4 R )‐(“ D ‐ lyxo ”)‐1,2,3,4‐alkanetetrol‐type products 4 predominate.